GoExpirely

The Problem

Small trucking operations — owner-operators and fleets of 5–20 trucks — face constant regulatory pressure from the DOT and FMCSA. CDLs expire. Medical certificates lapse every 1–2 years. Annual vehicle inspections come due. Missing any of these means fines, out-of-service orders, and lost revenue.

Large carriers have compliance departments. Small fleets don’t. They rely on calendar reminders, spreadsheets, and memory — all of which fail under the pressure of day-to-day operations.

What I Built

GoExpirely is a compliance tracking platform that gives small fleets the same visibility that large carriers have, without the overhead.

Core features:

• Document upload with AI parsing: Drivers upload their CDL, medical certificate, or inspection report. Claude extracts the expiry date directly from the document — no manual entry
• Fleet dashboard: A single view of every driver’s compliance status — green, amber (expiring soon), red (expired or missing)
• Automated reminders: Email and SMS alerts sent at configurable intervals before expiration (60 days, 30 days, 7 days)
• Driver self-service: Drivers can upload renewals themselves, reducing admin load on fleet managers
• Audit trail: Every document upload and status change is logged for FMCSA audit readiness

Technical Decisions

The AI document parsing is the core technical differentiator. Instead of building OCR from scratch or integrating a heavyweight document processing pipeline, I use Claude’s vision capabilities to read PDFs and images of government-issued documents and extract structured data (expiry date, document type, issuing state).

This approach is remarkably robust: Claude handles poor scans, rotated documents, different state formats, and handwritten renewal stamps without additional training or rule-based parsing.

Vue.js drives the dashboard with reactive status updates. Astro handles the marketing site and public-facing content. PostgreSQL stores fleet and document data with a schema designed around compliance windows and notification queues processed by Express workers.

AI: Document Intelligence + In-App Compliance Chatbot

Document to Database

When a driver uploads a document, Claude doesn’t just read the expiry date — it extracts a full structured record and populates the database directly:

• document_type: CDL / Medical Certificate / Annual Inspection Report
• expiry_date: extracted from any format, including handwritten renewal stamps
• issuing_state: from the document header or issuing authority
• license_number: for CDLs and medical cert holder IDs
• vehicle_unit: for inspection reports tied to a specific truck

This means a driver takes a photo of their medical card, uploads it, and GoExpirely creates or updates their compliance record without any manual entry — not even a date field to fill in. The AI handles the variance between a Texas DPS CDL, a Florida DOT medical card, and a DOT inspection form from 1996.

In-App Compliance Chatbot

Fleet managers don’t always know what the rules are — they know they need to stay compliant. GoExpirely includes a context-aware chatbot (powered by Claude) trained on DOT/FMCSA regulations that answers questions directly inside the dashboard:

• “How many days before expiry do I need to renew a medical certificate?”
• “My driver’s CDL expired yesterday — can he still drive while the renewal is processing?”
• “What happens if we get audited and a driver’s inspection report is missing?”

The chatbot returns cited, accurate answers in plain English — not a link to a 200-page CFR document.

Impact

The time savings are concrete: instead of a fleet manager manually checking every CDL and certificate each week, GoExpirely surfaces only what needs attention. A fleet of 10 drivers goes from ~2 hours of weekly compliance review to a 5-minute dashboard check.